A Novel Bis‐Thiourea Organocatalyst for the Asymmetric Aza‐Henry Reaction

Abstract

A novel bis-thiourea BINAM-based catalyst for the asymmetric aza-Henry reaction has been developed. This catalyst promotes the reaction of N-Boc imines with nitroalkanes to afford β-nitroamines with good yields and high enantioselectivities. This catalyst has the advantage that it can be prepared in a single step from commercially available materials. A model is proposed for the catalyst action where the both components of the reaction are activated simultaneously by hydrogen bonding. Regardless of the mechanism, the success of the present catalyst demonstrates the potential of bis-thioureas as an interesting class of relatively unexplored catalysts.

The influence of stereochemistry on anion binding and transport

“…In addition, thiourea 4 was shown to catalyse the aza-Henry reaction of a Boc-protected imine, again with a slight asymmetric induction (9). Receptor 2 has also been previously reported (10).…”

Rhodium(III)-Catalyzed Addition of Indoles with Boc-Imines via C−H Bond Activation

“…AgSbF 6 , AgOTf, AgSO 3 CF 3 and [Cp*RhCl 2 ] 2 were purchased from Energy Chemical Co. and used without further purification. Substrate 1-(N,N-dimethylcarbamoyl) indoles 10 and N-boc imines [13][14][15][16][17][18] were synthesized according to published procedures.…”

Characterization and Antimicrobial Studies of Five Substituted Bis-Thioureas

“…Some example of bis-thiourea derivatives are N 3 , N 3' -bis (disubstituted)isophatalyl-bis(thiourea), bis(thiourea)hydrazide [13], 2,2'-diaminobinapthalene-bis(thiourea) [14] and (bis)thiourea polyamine [15] [16,17,18]. In 2011, 1,2-Bis(N'-benzoylthioureidothioureido)-4-cholorobenzene was reported by Yamin research group [19].…”